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The preparation of 3,3a,4,5‐tetrahydronaphth[1,2‐ c ]isoxazoles from dilithiated 1‐tetralone oxime and select aromatic aldehydes
Author(s) -
Vella Jarrett H.,
Patel Nidhi S.,
Meierhoefer Michelle A.,
Hilton Ebony J.,
Sober Carolyn L.,
Grant Bonnie J.,
Kramp Catherine R.,
Knight John D.,
Metz Clyde R.,
Beam Charles F.,
Pennington William T.,
Vanderveer Donald G.
Publication year - 2006
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570430210
Subject(s) - chemistry , tetralone , oxime , organic chemistry , medicinal chemistry
Dilithiated 1‐tetralone oxime was condensed with several electron enriched aromatic aldehydes, such as 4‐methoxybenzaldehyde or lithiated 4‐hydroxybenzaldehyde, followed by acid cyclization to new tetrahydronaphthisoxazoles, 3,3a,4,5‐tetrahydronaphth[1,2‐ c ]isoxazoles, with a trans geometry of the C 3 ‐H and C 3a ‐H protons that was confirmed by X‐ray single crystal analysis.